Why Didn’t Jamal “Gravy” Woolard Make It As A Rapper?

Critics and fans everywhere seem to be embracing Jamal “Gravy” Woolard’s big screen portrayal of Biggie in the new biopic Notorious, which opens today. To mainstream America, he’s a budding young thespian. But to the hip-hop world, Gravy is already well known as a 30-year-old failed rapper.

In honor of his new career taking off, we decided to examine his previous bid for hip-hop stardom. What went wrong? Check out the five biggest reasons below…

#5: HE WAS A WACK GHOSTWRITER
A lot of up-and-coming rappers get their feet wet by secretly ghostwriting lyrics for lazy MCs. But when you’re writing simplistic lyrics for a wack rapper who’s the laughing stock of the industry, you should probably avoid bragging about it in interviews. Even Bow Wow sounded aiight when Tip was writing his lyrics. Lil’ Flip written by Gravy? Not so much.

#4: HIS MANAGER WAS MORE GANGSTER THAN HE WAS
Having a well-known former drug dealer backing your career can definitely do good things for an aspiring rapper. But in Gravy’s case, it seemed like he was always overshadowed by his manager Fendi. The CEO of Gravy’s label Dirty Money is a well-liked, charismatic hustler who often reminds people that he was “close” with Biggie and Jay-Z back in the day. And despite flashing his guns for the DVD cameras, Gravy seems more like a tough talking Teddy Bear than the hardened criminal he portrays. We don’t believe you.

#3: HE WISHED HE WAS JAY-Z AND/OR BIGGIE.
Sure, knowing all of Big’s lyrics probably helped him get the role of a lifetime as an actor, but dropping lazy homage mixtapes like Without A Doubt/Still Ready To Die proved he was stuck in the shadow of New York rap’s previous generation. Rather than bringing the buzz back to Brooklyn, he always came off as a generic imitation of the ’90s rappers he grew up idolizing.

#2: HIS NAME IS “GRAVY”.
Seriously. And no, “It’s all Gravy!” is not a cool catch phrase.

#1: HE SHOT HIMSELF IN THE ASS.
On the evening of April 26, 2006, Gravy arrived at Hot 97’s Greenwich Village studio to do an interview with Funkmaster Flex. While walking into the station with the Dirty Money crew in tow, a shooting occurred, and Gravy ended up with a bullet in his buttocks. No matter—Gravy went inside and did the interview anyway. Well, it didn’t take police long to figure out that the person who gave him the flesh wound was actually a member of his own entourage. Whoops. As a result of the incident, Gravy was banned from Hot 97 and dropped from his deal at Warner Brothers. Next time someone tells you that all publicity is good publicity, tell ’em about Gravy.